Chlorosuccinimide → HCID 86724441, compound

HRID 2369542Notes

Reaction equation

HRID 2369542 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@@H:8]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[CH:18]([C:25]([F:28])([F:27])[F:26])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:41])C(=O)C1>C(#N)C>[C:1]([O:5][C:6](=[O:33])[NH:7][C@@H:8]([CH2:29][CH:30]([CH3:31])[CH3:32])[CH2:9][O:10][C:11]1[C:12]([Cl:41])=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[CH:18]([C:25]([F:28])([F:26])[F:27])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86724439HCID 86724439, compound

Product 1

HCID 86724441HCID 86724441, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of tert-butyl((2S)-4-methyl-1-((5-(trifluoromethyl)-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate (50 mg, 0.107 mmol) and NCS (14.31 mg, 0.107 mmol) in acetonitrile (12 mL) was heated to 60° C. under nitrogen atmosphere for 12 h. The solvent was removed under reduced pressure. The residue was partitioned between water (15 mL) and DCM (15 mL). The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to yield tert-butyl((2S)-1-((9-chloro-5-(trifluoromethyl)-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (51 mg, 0.092 mmol, 86% yield) as a yellow solid. LCMS (ESI) m/e 501.2 [(M+H)+, calcd for C24H29ClF3N2O4 501.2]; LC/MS retention time (Method D): tR=2.02 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water (15 mL) and DCM (15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95b98b881eec4d8eba1f35f11c14a08d
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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